The present invention relates to pyridazin-3-one derivatives, their use as herbicides, and intermediates for their production.
EP-A-0029123 discloses a process for the preparation of substituted anilines and novel substituted anilines. In particular, it teaches that certain substituted anilines obtained by this process are useful as important starting materials for the preparation of novel substituted pyridazin-3-one derivatives having herbicidal activity in postemergence application. These pyridazin-3-one derivatives are, however, different from those of the present invention in that they have a substituted phenoxyphenyl group as an essential structural element at position 2 of the pyridazinone ring and further have quite distinct substituents on the pyridazinone ring.
The present inventors have intensively studied to find a compound having excellent herbicidal activity. As a result, they have found that pyridazin-3-one derivatives represented by formula [1] as depicted below have excellent herbicidal activity, thereby completing the present invention.
Thus the present invention provides a compound of the formula: 
wherein R1 is C1-C3 haloalkyl; R2 and R3 are the same or different and are hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, or C1-C3 alkoxy C1-C3 alkyl; and Q is [Q-1], [Q-2], [Q-3], [Q-4], or [Q-5] of the formula: 
wherein X is hydrogen or halogen;
Y is halogen, nitro, cyano, or trifluoromethyl;
Z1 is oxygen, sulfur, or NH;
Z2 is oxygen or sulfur;
n is 0 or 1;
B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, OR10, SR10, SO2xe2x80x94OR10, N(R11)R12, SO2N(R11)R12, NR11(COR13), NR11(SO2R14), N(SO2R14)(SO2R15), N(SO2R14)(COR13), NHCOOR13, COOR10, CON(R11)R12, CSN(R11)R12, COR16, CR17xe2x95x90CR18COR16, CR17xe2x95x90CR18COOR13, CR17xe2x95x90CR18CON(R11)R12, CH2CHWCOOR13, CH2CHWCON(R11)R12, CR17xe2x95x90NOR33, CR17xe2x95x90NN(R11)R12, CR17(Z2xe2x80x94R34)2, OCO2R19, or OCOR19;
R4 is hydrogen or C1-C3 alkyl;
R5 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkylalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, cyano C1-C6 alkyl, C2-C8 alkoxyalkyl, C3-C8 alkoxyalkoxyalkyl, carboxy C1-C6 alkyl, (C1-C6 alkoxy)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy)C1-C4 alkoxy}carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl, CH2CON(R11)R12, CH2COON(R11)R12, CH(C1-C4 alkyl)CON(R11)R12, CH(C1-C4 alkyl)COON(R11)R12, C2-C8 alkylthioalkyl, or hydroxy C1-C6 alkyl;
R6 is C1-C6 alkyl, C1-C6 haloalkyl, formyl, cyano, carboxyl, hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl, (C1-C6 alkyl)carbonyloxy C1-C6 alkyl, (C1-C6 haloalkyl)carbonyloxy C1-C6 alkyl, (C1-C6 alkoxy)carbonyl, or (C1-C6 alkyl)carbonyl;
R7 is hydrogen or C1-C6 alkyl; and
R8 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, hydroxy C1-C6 alkyl, C2-C8 alkoxyalkyl, C3-C10 alkoxyalkoxyalkyl, (C1-C5 alkyl)carbonyloxy C1-C6 alkyl, (C1-C6 haloalkyl)carbonyloxy C1-C6 alkyl, carboxyl, carboxy C1-C6 alkyl, (C1-C8 alkoxy)carbonyl, (C1-C6 haloalkoxy)carbonyl, (C3-C10 cycloalkoxy)carbonyl, (C3-C8 alkenyloxy)carbonyl, (C3-C8 alkynyloxy)carbonyl, aminocarbonyl, (C1-C6 alkyl)aminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, (C1-C6 alkyl)aminocarbonyloxy C1-C6 alkyl, or di(C1-C6 alkyl)aminocarbonyloxy C1-C6 alkyl;
wherein R10 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, benzyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, cyano C1-C6 alkyl, C2-C8 alkoxyalkyl, C2-C8 alkylthioalkyl, carboxy C1-C6 alkyl, (C1-C8 alkoxy)carbonyl C1-C6 alkyl, (C1-C6 haloalkoxy)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy)C1-C4 alkoxy}carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl, (C1-C6 alkyl)carbonyl C1-C6 alkyl, (C1-C6 haloalkyl)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy)C1-C4 alkyl}carbonyl C1-C6 alkyl, (C3-C8 cycloalkyl)carbonyl C1-C6 alkyl, CH2CONxe2x80x94(R11)R12, CH2COON(R11)R12, CH(C1-C4 alkyl)CON(R11)R12, CH(C1-C4 alkyl)COON(R11)R12, {(C1-C6 alkoxy)carbonyl C1-C6 alkyl}oxycarbonyl C1-C6 alkyl, or hydroxy C1-C6 alkyl;
R11 and R12 are independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, cyano C1-C6 alkyl, C2-C8 alkoxyalkyl, C2-C8 alkylthioalkyl, carboxy C1-C6 alkyl, (C1-C6 alkoxy)carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy)C1-C4 alkoxy}carbonyl C1-C6 alkyl, or R11 and R12 are combined together to form tetramethylene, pentamethylene, or ethyleneoxyethylene;
R13 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, or C3-C6 alkenyl;
R14 and R15 are independently C1-C6 alkyl, C1-C6 haloalkyl, or phenyl optionally substituted with methyl or nitro;
R16 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C8 alkoxyalkyl, or hydroxy C1-C6 alkyl;
R17 and R18 are independently hydrogen or C1-C6 alkyl;
R19 is C1-C6 alkyl;
R33 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, cyano C1-C6 alkyl, or (C1-C6 alkoxy)carbonyl C1-C6 alkyl;
R34 is C1-C6 alkyl, or two R34""s are combined together to form (CH2)2 or (CH2)3; and
W is hydrogen, chlorine, or bromine,
(hereinafter referred to as the present compound(s)); and a herbicide containing it as an active ingredient.
The present invention also provides a compound of the formula: 
wherein R3 is as defined above, and Q1 is [Q1-1], [Q-2], [Q1-3], [Q-4], or [Q-5] of the formula: 
wherein X, Y, Z1, Z2, n, R4, R5, R7, and R8 are as defined above; B1 is hydrogen, halogen, nitro, cyano, OR27, SR27, SO2OR27, NR11(R12), SO2NR11(R12), NR11(COR13), NR11(SO2R14), N(SO2R14)(SO2R15), N(SO2R14)(COR13), NHCOOR13, COOR27, CONR11(R12), CSNR11(R12), CR17xe2x95x90CR18COOR13, CR17xe2x95x90CR18CONR11(R12), CH2CHWCOOR13, CH2CHWCONR11(R12), CR17xe2x95x90NOR33, CR17xe2x95x90NNR11(R12), CR17(Z2R34)2, OCO2R19, or OCOR19; R9 is C1-C6 alkyl, C1-C6 haloalkyl, cyano, carboxyl, hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl, (C1-C6 alkyl)carbonyloxy C1-C6 alkyl, (C1-C6 haloalkyl)carbonyloxy C1-C6 alkyl, (C1-C6 alkoxy)carbonyl, or (C1-C6 alkyl)carbonyl; wherein R19 is as defined above; R27 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, benzyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, cyano C1-C6 alkyl, C2-C8 alkoxyalkyl, C2-C8 alkylthioalkyl, carboxy C1-C6 alkyl, (C1-C8 alkoxy)carbonyl C1-C6 alkyl, (C1-C6 haloalkoxy)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy)C1-C4 alkoxy}carbonyl C1-C6 alkyl, (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl, CH2CON(R11)R12, CH2COON(R11)R12, CH(C1-C4 alkyl)CON(R11)R12, CH(C1-C4 alkyl)COON(R11)R12, {(C1-C6 alkoxy)carbonyl C1-C6 alkyl}oxycarbonyl C1-C6 alkyl, or hydroxy C1-C6 alkyl; and R11, R12, R13, R14, R15, R17, R18, R19, R33, R34, and Z2 are as defined above.
In the above definition of the present compounds, the respective substituents are exemplified as follows:
Examples of the C1-C3 haloalkyl represented by R1 include trifluoromethyl and chlorodifluoromethyl.
Examples of the C1-C3 alkyl represented by R2 and R3 include methyl, ethyl, and isopropyl.
Examples of the C1-C3 haloalkyl represented by R2 and R3 include trichloromethyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.
Examples of the C1-C3 alkoxy C1-C3 alkyl represented by R2 and R3 include methoxymethyl.
Examples of the halogen represented by X, Y, and B include chlorine, fluorine, bromine, or iodine.
Examples of the C1-C6 alkyl represented by R10 include methyl, ethyl, isopropyl, propyl, isobutyl, butyl, t-butyl, amyl, isoamyl, and t-amyl.
Examples of the C1-C6 haloalkyl represented by R10 include 2-chloroethyl, 3-chloropropyl, and 2,2,2-trifluoroethyl.
Examples of the C3-C8 cycloalkyl represented by R10 include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
Examples of the C3-C6 alkenyl represented by R10 include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.
Examples of the C3-C6 haloalkenyl represented by R10 include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.
Examples of the C3-C6 alkynyl represented by R10 include propargl, 1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.
Examples of the C3-C6 haloalkynyl represented by R10 include 4-bromo-2-butynyl.
Examples of the cyano C1-C6 alkyl represented by R10 include cyanomethyl.
Examples of the C2-C8 alkoxyalkyl represented by R10 include methoxymethyl, methoxyethyl, ethoxymethyl, and ethoxyethyl.
Examples of the C2-C8 alkylthioalkyl represented by R10 include methylthiomethyl.
Examples of the carboxy C1-C6 alkyl represented by R10 include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.
Examples of the (C1-C8 alkoxy)carbonyl C1-C6 alkyl represented by R10 include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-amyloxycarbonylethyl.
Examples of the (C1-C6 haloalkoxy)carbonyl C1-C6 alkyl represented by R10 include 2-chloroethoxycarbonylmethyl.
Examples of the {(C1-C4 alkoxy)C1-C4 alkoxy}carbonyl C1-C6 alkyl represented by R10 include methoxymethoxycarbonylmethyl and 1-methoxymethoxycarbonylethyl.
Examples of the (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl represented by R10 include cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl.
Examples of the (C1-C6 alkyl)carbonyl C1-C6 alkyl represented by R10 include methylcarbonylmethyl.
Examples of the (C1-C6 haloalkyl)carbonyl C1-C6 alkyl represented by R10 include chloromethylcarbonylmethyl.
Examples of the {(C1-C4 alkoxy)C1-C4 alkyl}carbonyl C1-C6 alkyl represented by R10 include 2-methoxyethylcarbonylmethyl.
Examples of the (C3-C8 cycloalkyl)carbonyl C1-C6 alkyl represented by R10 include cyclopentylcarbonylmethyl.
Examples of the {(C1-C6 alkoxy)carbonyl C1-C6 alkyl}oxycarbonyl C1-C6 alkyl represented by R10 include (ethoxycarbonyl)methoxycarbonylmethyl.
Examples of the C1-C6 alkyl represented by R11 and R12 include methyl, ethyl, propyl, butyl, isopropyl, and isobutyl.
Examples of the C1-C6 haloalkyl represented by R11 and R12 include chloroethyl and bromoethyl.
Examples of the C3-C6 alkenyl represented by R11 and R12 include allyl, 1-methyl-2-propenyl, and 3-butenyl.
Examples of the C3-C6 alkynyl represented by R11 and R12 include propargyl and 1-methyl-2-propynyl.
Examples of the cyano C1-C6 alkyl represented by R11 and R12 include cyanomethyl.
Examples of the C2-C8 alkoxyalkyl represented by R11 and R12 include methoxymethyl and ethoxyethyl.
Examples of the C2-C8 alkylthioalkyl represented by R11 and R12 include methylthiomethyl and methylthioethyl.
Examples of the carboxy C1-C6 alkyl represented by R11 and R12 include carboxymethyl and 1-carboxyethyl.
Examples of the (C1-C6 alkoxy)carbonyl C1-C6 alkyl represented by R11 and R12 include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-amyloxycarbonylethyl.
Examples of the (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl represented by R11 and R12 include cyclopentyloxycarbonylmethyl.
Examples of the {(C1-C4 alkoxy)C1-C4 alkoxy}carbonyl C1-C6 alkyl represented by R11 and R12 include methoxymethoxycarbonylmethyl and 1-methoxymethoxycarbonylethyl.
Examples of the C1-C6 alkyl represented by R13 include methyl, ethyl, propyl, butyl, amyl, isopropyl, isobutyl, and isoamyl.
Examples of the C1-C6 haloalkyl represented by R13 include 2,2,2-trifluoroethyl.
Examples of the C3-C8 cycloalkyl represented by R13 include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
Examples of the C3-C6 alkenyl represented by R13 include allyl.
Examples of the C1-C6 alkyl represented by R14 and R15 include methyl, ethyl, propyl, butyl, and isopropyl.
Examples of the C1-C6 haloalkyl represented by R14 and R15 include trifluoromethyl, 2,2,2-trifluoroethyl, 2-chloroethyl, chloromethyl, and trichloromethyl.
Examples of the phenyl optionally substituted by methyl or nitro, which is represented by R14 and R15, include phenyl, p-methylphenyl, 2-nitrophenyl, 3-nitrophenyl, and 4-nitrophenyl.
Examples of the C1-C6 alkyl represented by R16 include methyl, ethyl, propyl, butyl, amyl, isopropyl, isobutyl, t-butyl, isoamyl, and t-amyl.
Examples of the C1-C6 haloalkyl represented by R16 include chloromlethyl, dichloromethyl, bromomethyl, dibromomethyl, 1-chloroethyl, 1,1-dichloroethyl, 1-bromoethyl, and 1,1-dibromoethyl.
Examples of the C2-C6 alkenyl represented by R16 include vinyl, allyl, 1-propenyl, and 1-methyl-2-propenyl.
Examples of the C2-C6 haloalkenyl represented by R16 include 3,3-dichloro-2-propenyl and 3,3-dibromo-2-propenyl.
Examples of the C2-C6 alkynyl represented by R16 include ethynyl and 2-butynyl.
Examples of the C2-C6 haloalkynyl represented by R16 include 3-bromo-2-propynyl.
Examples of the C2-C8 alkoxyalkyl represented by R16 include methoxymethyl, ethoxymethyl, and isopropoxymethyl.
Examples of the hydroxy C1-C6 alkyl represented by R16 include hydroxymethyl.
Examples of the C1-C6 alkyl represented by R17 and R18 include methyl.
Examples of the C1-C6 alkyl represented by R19 include methyl and ethyl.
Examples of the C1-C6 alkyl represented by R33 include methyl and ethyl.
Examples of the C1-C6 haloalkyl represented by R33 include 2-chloroethyl.
Examples of the C3-C8 cycloalkyl represented by R33 include cyclopentyl.
Examples of the C3-C6 alkenyl represented by R33 include allyl.
Examples of the C3-C6 haloalkenyl represented by R33 include 2-chloro-2-propenyl.
Examples of the C3-C6 alkynyl represented by R33 include propargyl.
Examples of the C3-C6 haloalkynyl represented by R33 include 4-chloro-2-butynyl.
Examples of the cyano C1-C6 alkyl represented by R33 include 2-cyanoethyl and cyanomethyl.
Examples of the (C1-C6 alkoxy)carbonyl C1-C6 alkyl represented by R33 include ethoxycarbonylmethyl.
Examples of the C1-C6 alkyl represented by R34 include methyl and ethyl.
Examples of the C1-C3 alkyl represented by R4 include methyl.
Examples of the C1-C6 alkyl represented by R5 include methyl, ethyl, propyl, butyl, amyl, isopropyl, isobutyl, and isoamyl.
Examples of the C1-C6 haloalkyl represented by R5 include 2-chloroethyl, 2-bromoethyl, 3-chlorobutyl, 3-bromobutyl, difluoromethyl, and bromodifluoromethyl.
Examples of the C3-C8 cycloalkylalkyl represented by R5 include cyclopentylmethyl.
Examples of the C3-C6 alkenyl represented by R5 include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.
Examples of the C3-C6 haloalkenyl represented by R5 include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.
Examples of the C3-C6 alkynyl represented by R5 include propargyl, 1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.
Examples of the C3-C6 haloalkynyl represented by R5 include 3-iodo-2-propynyl and 3-bromo-2-propynyl.
Examples of the cyano C1-C6 alkyl represented by R5 include cyanomethyl.
Examples of the C2-C8 alkoxyalkyl represented by R5 include methoxymethyl, ethoxymethyl, and 1-methoxyethyl.
Examples of the C3-C8 alkoxyalkoxyalkyl represented by R5 include methoxyethoxymethyl.
Examples of the carboxy C1-C6 alkyl represented by R5 include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.
Examples of the (C1-C6 alkoxy)carbonyl C1-C6 alkyl represented by R5 include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-amyloxycarbonylethyl.
Examples of the {(C1-C4 alkoxy)C1-C4 alkoxy}carbonyl C1-C6 alkyl represented by R5 include methoxymethoxycarbonylmethyl and 1-methoxymethoxycarbonylethyl.
Examples of the (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl represented by R5 include cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl.
Examples of the C2-C8 alkylthioalkyl represented by R5 include methylthiomethyl.
Examples of the hydroxy C1-C6 alkyl represented by R5 include hydroxymethyl, hydroxyethyl, and hydroxypropyl.
Examples of the C1-C6 alkyl represented by R6 include methyl and ethyl.
Examples of the C1-C6 haloalkyl represented by R6 include bromomethyl, dibromomethyl, tribromomethyl, 1-bromoethyl, chloromethyl, dichloromethyl, and trichloromethyl.
Examples of the hydroxy C1-C6 alkyl represented by R6 include hydroxymethyl.
Examples of the C1-C6 alkoxy C1-C6 alkyl represented by R6 include methoxymethyl, ethoxymethyl, propoxymethyl, and isopropoxymethyl.
Examples of the C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl represented by R6 include methoxymethoxymethyl, methoxyethoxymethyl, and ethoxymethoxymethyl.
Examples of the (C1-C6 alkyl)carbonyloxy C1-C6 alkyl represented by R6 include acetyloxymethyl, ethylcarbonyloxymethyl, and isopropylcarbonyloxymethyl.
Examples of the (C1-C6 haloalkyl)carbonyloxy C1-C6 alkyl represented by R6 include trifluoroacetyloxymethyl, chloroacetyloxymethyl, and trichloroacetyloxymethyl.
Examples of the (C1-C6 alkoxy)carbonyl represented by R6 include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, amyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, and isoamyloxycarbonyl.
Examples of the (C1-C6 alkyl)carbonyl represented by R6 include methylcarbonyl, ethylcarbonyl, and isopropylcarbonyl.
Examples of the C1-C6 alkyl represented by R7 include methyl.
Examples of the C1-C6 alkyl represented by R8 include methyl and ethyl.
Examples of the C1-C6 haloalkyl represented by R8 include chloromethyl. bromomethyl, and fluoromethyl.
Examples of the C1-C6 hydroxyalkyl represented by R8 include hydroxymethyl.
Examples of the C2-C8 alkoxyalkyl represented by R8 include methoxymethyl, ethoxymethyl, isopropoxymethyl, butoxymethyl, and isobutoxymethyl.
Examples of the C3-C10 alkoxyalkoxyalkyl represented by R8 include methoxymethoxymethyl, methoxyethoxymethyl, and ethoxymethoxymethyl.
Examples of the (C1-C5 alkyl)carbonyloxy C1-C6 alkyl represented by R8 include acetyloxymethyl, ethylcarbonyloxymethyl, and isopropylcarbonyloxymethyl.
Examples of the (C1-C6 haloalkyl)carbonyloxy C1-C6 alkyl represented by R8 include 2-chloroethylcarbonyloxymethyl.
Examples of the carboxy C1-C6 alkyl represented by R8 include carboxymethyl.
Examples of the (C1-C8)alkoxycarbonyl represented by R8 include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, amyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, and isoamyloxycarbonyl.
Examples of the (C1-C6 haloalkoxy)carbonyl represented by R8 include 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 3-chlorobutoxycarbonyl, 1-chloro-2-propoxycarbonyl, 1,3-dichloro-2-propoxycarbonyl, 2,2-dichloroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, and 2,2,2-tribromoethoxycarbonyl.
Examples of the (C3-C10 cycloalkoxy)carbonyl represented by R8 include cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, and cyclohexyloxycarbonyl.
Examples of the (C3-C8 alkenyloxy)carbonyl represented by R8 include allyloxycarbonyl and 3-butenyloxycarbonyl.
Examples of the (C3-C8 alkynyloxy)carbonyl represented by R8 include propargyloxycarbonyl, 3-butynyloxycarbonyl, and 1-methyl-2-propynyloxycarbonyl.
Examples of the (C1-C6 alkyl)aminocarbonyl represented by R8 include methylaminocarbonyl, ethylaminocarbonyl, and propylaminocarbonyl.
Examples of the di(C1-C6 alkyl)aminocarbonyl represented by R8 include dimethylaminocarbonyl, diethylaminocarbonyl, and diisopropylaminocarbonyl.
Examples of the (C1-C6 alkyl)aminocarbonyloxy C1-C6 alkyl represented by R8 include methylaminocarbonyloxymethyl, ethylaminocarbonyloxymethyl, and propylaminocarbonyloxymethyl.
Examples of the di(C1-C6 alkyl)aminocarbonyloxy C1-C6 alkyl represented by R8 include dimethylaminocarbonyloxyalkyl and diethylaminocarbonyloxyalkyl.
In the present compounds, preferred substituents from the viewpoint of their herbicidal activity are as follows:
R1 is preferably methyl substituted with one or more fluorine atoms, such as trifluoromethyl or chlorodifluoromethyl, or ethyl substituted with one or more fluorine atoms, such as pentafluoroethyl, and more preferably trifluoromethyl;
R2 is preferably C1-C3 alkyl such as methyl or ethyl, or hydrogen, and more preferably methyl or hydrogen;
R3 is preferably C1-C3 alkyl such as methyl or ethyl, or hydrogen, and more preferably methyl or hydrogen; and
Q is preferably [Q-1], [Q-2], [Q-3], or [Q-4].
Preferred examples of the present compounds from the viewpoint of their herbicidal activity are those which contain the above preferred substituents in combination.
When Q is [Q-1], more preferred compounds are those wherein X is hydrogen or fluorine and Y is chlorine. Among these compounds are more preferred ones wherein B is OR10, SR10, N(R11)R12, NR11(SO2R14), or COOR10. Among these compounds are more preferred ones wherein R10 is C1-C6 alkyl, C3-C6 alkynyl, (C1-C8 alkoxy)carbonyl C1-C6 alkyl, or (C3-C8 cycloalkoxy)carbonyl C1-C6 alkyl; R11 is hydrogen; R12 is (C1-C6 alkoxy)carbonyl C1-C6 alkyl; and R14 is C1-C6 alkyl or C1-C6 haloalkyl.
When Q is [Q-2], more preferred compounds are those wherein X is fluorine or hydrogen; Z1 is oxygen; R4 is hydrogen; and n is 1. Among these compounds are more preferred ones wherein R5 is C3-C6 alkynyl.
Typical examples of the preferred compounds are as follows:
7-Fluoro-6-(5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;
7-Fluoro-6-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;
6-(5-Trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;
6-(4Methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;
2-(4-Chloro-2-fluoro-5-isopropoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one;
2-(4-Chloro-2-fluoro-5-methoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one;
2-(4-Chloro-2-fluoro-5-ethoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one;
2-(4-Chloro-2-fluoro-5-propargyloxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one;
Methyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;
Ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;
Propyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;
Isopropyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;
Butyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;
Pentyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;
Cyclopentyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;
Ethyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate;
Methyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate;
Ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate;
Methyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate;
Ethyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate;
Methyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate;
Methyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate;
Ethyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate;
Ethyl 2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate;
Methyl 2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate;
Ethyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate;
Methyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate;
Isopropyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-y)phenylthio}propionate;
Ethyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylamino}propionate;
Ethyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylamino}propionate;
N-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl}methanesulfonamide;
N-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl}chloromethanesulfonamide;
N-{2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl}methanesulfonamide;
Methyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate;
Ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate;
Ethyl 2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate;
Isopropyl 2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate; and
2-(4-Chloro-2-fluoro-5-propargyloxyphenyl)-6-methyl-5-trifluoromethylpyridazin-3-one.
Among these compounds, more preferred ones from the viewpoint of their herbicidal activity are as follows:
7-Fluoro-6-(5-trifluoromethyl-3-pyridazinon-2-yl)-4-proparygyl-2H-1,4-benzoxazin-3-one,
7-Fluoro-6-(4-methyl-5-trifluoromethyl-3-pyrdazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;
6-(4-Methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;
Ethyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyrizazinon-2-yl)phenoxy}propionate; and
Ethyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate.
In addition, more preferred ones from the viewpoint of their selectivity between crop plants and undesired weeds are as follows:
2-(4-Chloro-2-fluoro-5-propargyloxyphenyl)-4-methyl-5-trifluoromethylpyrizazin-3-one;
Ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;
N-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl}methanesulfonamide; and
Ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate.
The present compounds can be produced, for example, according to the production processes described below.
This is the production process in which among the present compounds, a compound of the formula: 
wherein R1, R2, R3, and Q1 are as defined above, is produced by reacting a hydrazone derivative of the formula: 
wherein R1, R3, and Q1 are as defined above, with a compound of the formula: 
wherein R2 is as defined above; R28 is C1-C6 alkyl such as methyl or ethyl; and Ar is an optionally substituted phenyl such as phenyl.
The reaction is usually effected in a solvent. The reaction temperature is usually in the range of xe2x88x9220xc2x0 to 150xc2x0 C., preferably 0xc2x0 to 100xc2x0 C. The reaction time is usually in the range of a moment to 72 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of compound [5] to 1 mole of compound [4] is ideal, can be freely changed depending upon the reaction conditions.
Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran (THF), and ethylene glycol dimethyl ether; nitro compounds such as nitromethane and nitrobenzene; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; water; and mixtures thereof.
After completion of the reaction, the reaction solvent is distilled out from the reaction mixture and the residue is subjected to chromatography, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as chromatography or recrystallization. Thus the desired compound of the present invention can be isolated.
The above reaction is effected through a compound of the formula: 
wherein R1, R2, R3, R28, and Q1 are as defined above.
This production process can also be conducted by isolating compound [6] and effecting intramolecular cyclization of compound [6]. The cyclization can usually be effected in a solvent. The reaction temperature is usually in the range of xe2x88x9220xc2x0 to 150xc2x0 C., preferably 50xc2x0 to 150xc2x0 C. The reaction time is usually in the range of a moment to 72 hours.
Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; fatty acids such as formic acid, acetic acid, and propionic acid; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; water; and mixtures thereof.
As the reaction catalyst, acids such as sulfuric acid or bases such as sodium methylate can be used.
This is the production process according to the following scheme: 
wherein R51 is a substituent other than hydrogen, which is included in the definition of R5; R1, R2, R3, R4, and X are as defined above; R22 is C1-C6 alkyl; and D is chlorine, bromine, iodine, methanesulfonyloxy, trifluoromethanesulfonyloxy, or p-toluenesulfonyloxy.
Process for Producing Compound [8]from Compound [7]
Compound [8] can be produced by reacting compound [7] with a nitrating agent in a solvent.
Nitrating agent: nitric acid or the like
Amount of nitrating agent: 1 to 10 moles per mole of compound [7]
Solvent: sulfuric acid
Temperature: xe2x88x9210xc2x0 C. to room temperature
Time: a moment to 24 hours
Process for Producing Compound [9] from Compound [8]
Compound [9] can be produced by reacting compound [8] with a compound of the formula: 
wherein R4 and R22 are as defined above, in the presence of potassium fluoride in a solvent.
Amount of compound [12]: 1 to 50 moles per mole of compound [8]
Amount of potassium fluoride: 1 to 50 moles per mole of compound [8]
Solvent: 1,4-dioxane or the like
Temperature: room temperature to refluxing temperature under heating
Time: a moment to 96 hours
Process for Producing Compound [10] from Compound [9]
Compound [10] can be produced by reducing compound [9] with iron powder or the like in the presence of an acid in a solvent.
Amount of iron powder: 3 moles to an excess per mole of compound [9]
Acid: acetic acid or the like
Amount of acid: 1 to 10 moles
Solvent: water, ethyl acetate, or the like
Temperature: room temperature to refluxing temperature under heating
Time: a moment to 24 hours
Process for Producing Compound [11] from Compound [10]
Compound [11] can be produced by reacting compound [10] with a compound of the formula:
xe2x80x83R51xe2x80x94Dxe2x80x83xe2x80x83[13]
wherein R51 and D are as defined above.
The reaction is usually effected in the presence of a base in a solvent. The reaction temperature is usually in the range of xe2x88x9220xc2x0 to 150xc2x0 C., preferably 0xc2x0 to 50xc2x0 C. The reaction time is usually in the range of a moment to 48 hours. The amounts of the reagents to be used in the reaction are usually 1 to 3 moles of compound [13] and usually 1 to 2 moles of the base, per mole of compound [10].
Examples of the base which can be used include inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate, and sodium carbonate; and organic bases such as triethylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, N,N-dimethylaniline, and N,N-diethylaniline.
Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; nitro compounds such as nitrobenzene; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylamine, N,N-diethylaniline, and N-methylmorpholine; and mixtures thereof.
After completion of the reaction, the reaction mixture is poured into water, if necessary, and subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the present compound [11] can be obtained.
The above compound [9] can also be produced according to the following scheme: 
wherein R1, R2, R3, R4, R22, and X are as defined above.
Process for Producing Compound [15] from Compound [14]
Compound [15] can be produced by reacting compound [14] with a compound of the formula: 
wherein R4 and R22 are as defined above, in the presence of a base in a solvent.
Amount of compound [17]: 1 to 2 moles per mole of compound [14]
Base: sodium hydride, sodium carbonate, or the like
Amount of base: 1 to 2 moles per mole of compound [14]
Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like
Temperature: 0xc2x0 to 100xc2x0 C.
Time: a moment to 24 hours
Process for Producing Compound [9] from Compound [15]
Compound [9] can be produced by reacting compound [15] with a nitrating agent in a solvent.
Nitrating agent: nitric acid or the like
Amount of nitrating agent: 1 to 10 moles per mole of compound [15]
Solvent: sulfuric acid, acetic-acid, or the like
Temperature: xe2x88x9210xc2x0 C. to room temperature
Time: a moment to 24 hours
Process for Producing Compound [16] from Compound [14]
Compound [16] can be produced by reacting compound [14] with a nitrating agent in a solvent.
Nitrating agent: nitric acid or the like
Amount of nitrating agent: 1 to 10 moles per mole of compound [14]
Solvent: sulfuric acid, acetic acid, or the like
Temperature: xe2x88x9210xc2x0 C. to room temperature
Time: a moment to 24 hours
Process for Producing Compound [9] from Compound [16]
Compound [9] can be produced by reacting compound [16] with compound [17] in the presence of a base in a solvent.
Amount of compound [17]: 1 to 2 moles per mole of compound [16]
Base: sodium hydride, potassium carbonate, or the like
Amount of base: 1 to 2 moles per mole of compound [16]
Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like
Temperature: 0xc2x0 to 100xc2x0 C.
Time: a moment to 24 hours
This is the production process according to the following scheme: 
wherein X, R1, R2, R3, R51, and D are as defined above.
Process for Producing Compound [19] from Compound [18]
Compound [19] can be produced by reducing compound [18] with iron powder or the like in the presence of an acid in a solvent.
Amount of iron powder: 3 moles to an excess per mole of compound [18]
Acid: acetic acid or the like
Amount of acid: 1 to 10 moles per mole of compound [18]
Solvent: water, ethyl acetate, or the like
Temperature: room temperature to refluxing temperature under heating
Time: a moment to 24 hours
Process for Producing Compound [21] from Compound [20]
Compound [20] can be produced by reacting compound [19] with sodium thiocyanate, potassium thiocyanate, or the like in a solvent, and then reacting it with bromine or chlorine in a solvent.
Amount of sodium thiocyanate, potassium thiocyanate, or the like: 1 to 10 moles per mole of compound [19]
Amount of bromine or chlorine: 1 to 10 moles per mole of compound [19]
Solvent: aqueous hydrochloric acid, aqueous acetic acid, aqueous sulfuric acid, or the like
Temperature: 0xc2x0 to 50xc2x0 C.
Time: a moment to 150 hours
Process for Producing Compound [21] from Compound [20]
Compound [21] can be produced by 1) reacting compound [20] with sodium nitrite, potassium nitrite, or the like in a solvent, and then 2) heating it in an acidic solution.
 less than Reaction 1) greater than 
Amount of sodium nitrite, potassium nitrite, or the like: 1 to 2 moles per mole of compound [20]
Solvent: aqueous hydrochloric acid or aqueous sulfuric acid
Temperature: xe2x88x9210xc2x0 to 10xc2x0 C.
Time: a moment to 5 hours
 less than Reaction 2) greater than 
Acidic solution: aqueous hydrochloric acid, aqueous sulfuric acid, or the like
Temperature: 70xc2x0 C. to refluxing temperature under heating
Time: a moment to 24 hours
Process for Producing Compound [22] from Compound [21]
Compound [22] can be produced by reacting compound [21] with compound [13] in the presence of a base in a solvent.
Amount of compound [13]: 1 to 3 moles per mole of compound [21]
Base: sodium hydride, potassium carbonate, or the like
Amount of base: 1 to 2 moles per mole of compound [21]
Solvent: 1,4-dioxane, N,N-dimethylforrnaide, or the like
Temperature: 0xc2x0 to 100xc2x0 C.
Time: a moment to 48 hours
This is the production process according to the following scheme: 
wherein X, R1, R2, R3, and R5 are as defined above.
Process for Producing Compound [24] from Compound [23]
Compound [24] can be produced by reducing compound [23] with iron powder or the like in the presence of an acid in a solvent.
Amount of iron powder: 3 moles to an excess per mole of compound [23]
Acid: acetic acid or the like
Amount of acid: 1 to 10 moles per mole of compound [23]
Solvent: water, ethyl acetate, or the like
Temperature: room temperature to refluxing temperature under heating
Time: a moment to 24 hours
Process for Producing Compound [25] from Compound [24]
Compound [25] can be produced by 1) reacting compound [24] with a nitrite salt in a solvent to form a diazonium salt, and then 2) raising the temperature to cause the cyclization of the diazonium salt in a solvent.
 less than Reaction 1) greater than 
Nitrite salt: sodium nitrite, potassium nitrite, or the like
Amount of nitrite salt: 1 to 2 moles per mole of compound [24]
Solvent: aqueous hydrochloric acid aqueous sulfuric acid, or the like
Temperature: xe2x88x9210xc2x0 to 10xc2x0 C.
Time: a moment to 5 hours
 less than Reaction 2) greater than 
Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like
Temperature: room temperature to 80xc2x0 C.
Time: a moment to 24 hours
This is the production process according to the following scheme: 
wherein Y1 is a substituent other than nitro, which is included in the definition of Y; R101 is a substituent other than hydrogen, which is included in the definition of R10; and X, R1, R2, and R3 are as defined above.
Process for Producing Compound [27] from Compound [26]
Compound [27] can be produced by adding nitric acid to compound [26] in a solvent (see Organic Synthesis Collective, Vol. 1, p. 372).
The reaction temperature is usually in the range of 0xc2x0 to 100xc2x0 C. The reaction time is usually in the range of a moment to 24 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of nitric acid to 1 mole of compound [26] is ideal, can be freely changed depending upon the reaction conditions.
Examples of the solvent which can be used include acidic solvents such as sulfuric acid.
Process for Producing Compound [28] from Compound [27]
Compound [28] can be produced by reducing compound [27] in a solvent (see Organic Synthesis Collective, Vol. 2, p. 471, and ibid., Vol. 5, p. 829).
For example, the production can be achieved by adding compound [27], which is neat or dissolved in a solvent such as ethyl acetate, to a mixture of acetic acid, iron powder, and water. The reaction temperature is usually in the range of 0xc2x0 to 100xc2x0 C. The reaction time is usually in the range of a moment to 24 hours.
After completion of the reaction, the reaction mixture is filtered to collect the crystals, which may be precipitated by the addition of water, if necessary, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.
Process for Producing Compound [29] from Compound [28]
Compound [29] can be produced by 1) reacting compound [28] with a nitrite salt in a solvent, and then 2) heating it in an acidic solvent.
 less than Reaction 1) greater than 
Nitrite salt: sodium nitrite, potassium nitrite, or the like
Amount of nitrite salt: 1 to 2 moles per mole of compound [28]
Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like
Temperature: xe2x88x9210xc2x0 to 10xc2x0 C.
Time: a moment to 5 hours
 less than Reaction 2) greater than 
Acidic solvent: aqueous hydrochloric acid or aqueous sulfuric acid
Temperature: 70xc2x0 C. to refluxing temperature under heating
Time: a moment to 24 hours.
Process for Producing Compound [30] from Compound [29]
Compound [30] can be produced by reacting compound [29] with a compound of the formula:
R10xe2x80x94Dxe2x80x83xe2x80x83[31]
wherein R10 and D are as defined above, in the presence of a base in a solvent.
The reaction is usually effected in a solvent. The reaction temperature is usually in the range of xe2x88x9220xc2x0 to 150xc2x0 C., preferably 0xc2x0 to 100xc2x0 C. The reaction time is usually in the range of a moment to 72 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of compound [31] and 1 mole of a base to 1 mole of compound [29] is ideal, can be freely changed depending upon the reaction conditions.
Examples of the base which can be used include organic bases and inorganic bases such as potassium carbonate, sodium hydroxide, and sodium hydride.
Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof.
After completion of the reaction, the reaction mixture is filtered to collect the crystals, which may be precipitated by the addition of water, if necessary, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.
This is the production process according to the following scheme: 
wherein R23 and R24 are independently a substituent other than hydrogen, which is included in the definition of R11 and R12; or COR13, SO2R14, SO2R15, or COOR10, wherein R10, R13, R14, and R15 are as defined above; X, Y1, R1, R2, and R3 are as defined above.
Process for Producing Compound [32] from Compound [28]
Compound [32] can be produced by reacting compound [28] with a compound of the formula:
R20xe2x80x94Dxe2x80x83xe2x80x83[34]
wherein R20 is a substituent other than hydrogen, which is included in the definition of R11 or R12; or COR13, SO2R14, SO2R15, or COOR10, wherein R10, R13, R14, and R15 are as defined above; and D is as defined above; or with a compound of the formula:
(R21 )2Oxe2x80x83xe2x80x83[35]
wherein R21 is COR13, SO2R14, SO2R15, or COOR10, wherein R10, R13, R14, and R15 are as defined above, usually in the presence of a base and usually in a solvent.
The reaction temperature is usually in the range of xe2x88x9220xc2x0 to 200xc2x0 C., preferably 0xc2x0 to 180xc2x0 C. The reaction time is usually in the range of a moment to 72 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of compound [34] or [35] to 1 mole of compound [28] is ideal, can be freely changed depending upon the reaction conditions.
Examples of the base which can be used include organic bases such as pyridine and triethylamine, and inorganic bases.
Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitrites such as acetonitrile and isobutyronitrile; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such; as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof.
After completion of the reaction, the reaction mixture is filtered to collect the precipitated crystals, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.
Process for Producing Compound [33] from Compound [32]
Compound [33] can be produced by reacting compound [32] with compound [34] or [35]. This production process is based on the process for producing compound [32] from compound [28].
This is the production process according to the following scheme: 
wherein X, Y R1, R2, R3, R10, R11, and R12 are as defined above.
Process for Producing Compound [37] from Compound [36]
Compound [37] can be produced by reacting compound [36] with chlorosulfonic acid without any solvent or in a solvent.
Amount of chlorosulfonic acid: 1 mole to an excess per mole of compound [36]
Solvent: sulfuric acid
Temperature: 0xc2x0 to 70xc2x0 C.
Time: a moment to 24 hours
(see Org. Syn. Coll., Vol. 1, 8 (1941))
Process for Producing Compound [38] from Compound [37]
Compound [38] can be produced by reacting compound [37] with a compound of the formula:
R10xe2x80x94OHxe2x80x83xe2x80x83[40]
wherein R10 is as defined above, in the presence of a base without any solvent or in a solvent.
Amount of compound [24]: 1 mole to an excess per mole of compound [37]
Base: organic bases such as triethylamine or inorganic bases such as potassium carbonate
Amount of base: 1 to 2 moles per mole of compound [37]
Solvent: N,N-dimethylformamide, 1,4-dioxane, or the like
Temperature: 0xc2x0 to 100xc2x0 C.
Time: a moment to 24 hours
Process for Producing Compound [39] from Compound [37]
Compound [39] can be produced by reacting compound [37] with a compound of the formula:
xe2x80x83R11R12NHxe2x80x83xe2x80x83[41]
wherein R11 and R12 are as defined above, in the presence or absence of a base without any solvent or in a solvent.
Amount of compound [41]: 1 mole to an excess per mole of compound [37]
Base: organic bases such as triethylamine or inorganic bases such as potassium carbonate
Amount of base: 1 to 2 moles per mole of compound [37]
Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like
Temperature: 0xc2x0 to 10xc2x0xc2x0 C.
Time: a moment to 24 hours
This is the production process according to the following scheme: 
wherein X, Y, R1, R2, R3, R11, R12, R17, R18, and R22 are as defined above.
Process for Producing Compound [43] from Compound [42]
Compound [43] can be produced from compound [42] according to the method described in JP-A 5-294920/1993, pp. 15-16.
Process for Producing Compound [44] from Compound [43]
Compound [44] can be produced by reacting compound [43] with a compound of the formula:
(C6H5)3Pxe2x95x90CR18COOR22xe2x80x83xe2x80x83[45]
or
(C2H5O)2P(O)CHR18COOR22xe2x80x83xe2x80x83[46]
wherein R18 and R22 are as defined above, in a solvent, and when compound [46] is used, in the presence of a base.
Amount of compound [45] or [46]: 1 to 2 moles per mole of compound [43]
Solvent: tetrahydrofuran, toluene, or the like
Base: sodium hydride or the like
Amount of base: 1 to 2 moles per mole of compound [43]
Temperature: 0xc2x0 to 50xc2x0 C.
Time: a moment to 24 hours
Process for Producing Compound [45] from Compound [44]
Compound [45] can be produced by reacting compound [44] with compound [41].
This is the production process according to the following scheme: 
wherein W2 is chlorine or bromine; and X, Y, R1, R2, R3, and R13 are as defined above.
The reaction conditions are described, for example, in U.S. Pat. No. 5,208,212.
The production can be achieved by converting compound [48] into a diazonium salt in a solution of hydrochloric acid, hydrobromic acid, or the like according to the ordinary method, and then reacting it with a compound of the formula:
CH2xe2x95x90CHCO2R13xe2x80x83xe2x80x83[50]
wherein R13 is as defined above, in the presence of a copper salt, such as, copper(II)chloride or copper(II)bromide, in a solvent such as acetonitrile.
The reaction temperature is usually in the range of xe2x88x9220xc2x0 to 150xc2x0 C., preferably 0xc2x0 to 60xc2x0 C. The reaction time is usually in the range of a moment to 72 hours.
After completion of the reaction, the reaction mixture is filtered to collect the crystals, which may be precipitated by the addition of water, if necessary, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.
This is the production process according to the following scheme: 
wherein W3 is bromine or iodine and X, Y1, R1, R2, R3, and R13 are as defined above.
Process for Producing Compound [51] from Compound [28]
Compound [51] can be produced by 1) making a diazonium salt from compound [28] in a solvent and then 2) reacting it with potassium iodide or copper(I)bromide in a solvent.
 less than Reaction 1) greater than 
Diazotizing agent: sodium nitrite, potassium nitrite, or the like.
Amount of diazotizing agent: 1 to 2 moles per mole of compound [28]
Solvent: aqueous hydrogen bromide, aqueous sulfuric acid, or the like.
Temperature: xe2x88x9210xc2x0 to 10xc2x0 C.
Time: a moment to 5 hours
 less than Reaction 2) greater than 
Amount of potassium iodide or copper(I)bromide: 1 mole to an excess per mole of compound [28]
Solvent: aqueous hydrogen bromide, aqueous sulfuric acid, or the like
Temperature: 0xc2x0 to 80xc2x0 C.
Time: a moment to 24 hours
(see Org. Syn. Coll., Vol. 2, 604 (1943), and ibid., Vol. 1, 136 (1941))
Process for Producing Compound [52] from Compound [51]
Compound [52] can be produced by reacting compound [51] with a compound of the formula:
R13xe2x80x94OHxe2x80x83xe2x80x83[53]
wherein R13 is as defined above, in the presence of a transition metal catalyst and a base in a solvent under an atmosphere of carbon monoxide.
Catalyst: PdCl2(PPh3)2 or the like
Amount of catalyst: a catalytic amount to 0.5 mole per mole of compound [51]
Amount of compound [53]: 1 mole to an excess per mole of compound [51]
Base: organic bases such as diethylamine
Amount of base: 1 to 2 moles per mole of compound [51]
Solvent: N,N-dimethylformamide or the like
Pressure of carbon monoxide: 1 to 150 atm.
Temperature: 0xc2x0 to 100xc2x0 C.
Time: a moment to 72 hours
(see Bull. Chem. Soc. Jpn., 48 (7) 2075 (1975))
This is the production process according to the following scheme: 
wherein X, Y, R1, R2, R3, and R19 are as defined above.
Compound [55] can be produced by hydrolyzing compound [54] in an acid solvent such as sulfuric acid, or in the presence of an acid such as boron tribromide in a solvent such as methylene chloride.
The reaction temperature is usually in the range of xe2x88x9220xc2x0 to 150xc2x0 C., preferably 0xc2x0 to 100xc2x0 C. The reaction time is usually in the range of a moment to 72 hours.
The amount of the acid to be used in the reaction, although the proportion of 1 mole of the acid to 1 mole of compound [54] is ideal, can be freely changed depending upon the reaction conditions.
After completion of the reaction, the reaction mixture is filtered to collect the crystals, which may be precipitated by the addition of water, if necessary, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.
This is the production process according to the following scheme: 
wherein X, Y, R1, R2, R3, Z2, and R17 are as defined above; Z3 is oxygen or sulfur; R25 is hydrogen or C1-C5 alkyl; and R26 is C1-C6 alkyl, C3-C6 alkenyl, or C3-C6 alkynyl.
Compound [57] can be produced by reacting compound [56] with a compound of the formula:
R26Z3Hxe2x80x83xe2x80x83[58]
wherein R26 and Z3 are as defined above, in the presence or absence of a catalyst and usually in a solvent.
The amount of compound [58] to be used in the reaction, although the proportion of 1 mole of compound [58] to 1 mole of compound [56] is ideal, can be freely changed depending upon the reaction conditions.
Examples of the catalyst which can be used include p-toluenesulfonic acid. Examples of the solvent which can be used include toluene, xylene or the like, or compound [56].
The reaction temperature is usually in the range of 0xc2x0 to 200xc2x0 C., preferably 50xc2x0 to 150xc2x0 C. The reaction time is usually in the range of a moment to 72 hours.
After completion of the reaction, the reaction mixture is filtered to collect the crystals, which may be precipitated by the addition of water, if necessary, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.
This is the production process according to the following scheme: 
wherein R61 is a substituent other than methyl, which is included in the definition of R6; and X, Y, R1, R2, and R3 are as defined above.
Process for Producing Compound [59] from Compound [55]
Compound [59] can be produced by reacting compound [55] with 2,3-di-chloropropene in the presence of a base in a solvent.
Amount of 2,3-dichloropropene: 1 to 3 moles per mole compound [55]
Base: inorganic bases such as potassium carbonate
Amount of base: 1 to 2 moles per mole of compound [55]
Solvent: N,N-dimethylformamide or the like
Temperature: 0xc2x0 to 70xc2x0 C.
Time: a moment to 24 hours
Process for Producing Compound [60] from Compound [59]
Compound [60] can be produced by heating compound [59] in a solvent.
Solvent: N,N-dimethylformamide, N,N-dimethylaniline, N,N-diethylaniline, p-diisopropylbenzene, or the like
Temperature: 70xc2x0 to 200xc2x0 C.
Time: a moment to 24 hours
Process for Producing Compound [61] from Compound [60]
Compound [61] can be produced from compound [62] according to the method in which the methyl group in position 2 on the benzofuran ring is replaced with another substituent, as described in U.S. Pat. No. 5,308,829, columns 2-11.
This is the production process according to the following scheme: 
wherein X, Y, R1, R2, R3, and R7 are as defined above.
Process for Producing Compound [62] from Compound [55]
Compound [62] can be produced by reacting compound [55] with a compound of the formula:
xe2x80x83CH2xe2x95x90CR7CH2W2xe2x80x83xe2x80x83[65]
wherein W2 and R7 are as defined above, in the presence of a base in a solvent.
Amount of compound [65]: 1 to 5 moles per mole of compound [55]
Base: inorganic bases such as potassium carbonate
Amount of base: 1 to 2 moles per mole of compound [55]
Solvent: N,N-dimethylformamide, 1,4-dioxane, or the like
Temperature: 0xc2x0 to 70xc2x0 C.
Time: a moment to 24 hours
Process for Producing Compound [63] from Compound [62]
Compound [64] can be produced by heating compound [62] in a solvent.
Solvent: N,N-dimethylaniline, N,N-diethylaniline, p-diisopropylbenzene, or the like
Temperature: 100xc2x0 to 200xc2x0 C.
Time: a moment to 24 hours
Process for Producing Compound [64] from Compound [63]
Compound [64] can be produced by heating compound [63] in the presence of an acid in a solvent.
Acid: organic acids such as p-toluenesulfonic acid; and inorganic acids such as sulfuric acid
Amount of acid: a catalytic amount to 1 mole per mole of compound [63]
Solvent: toluene, xylene, or the like
Temperature: 100xc2x0 to 250xc2x0 C.
Time: a moment to 24 hours
This is the production process according to the following scheme: 
wherein R81 is a substituent other than methyl and hydroxymethyl, which is included in the definition of R8; and X, Y, R1, R2, R3, and R7 are as defined above.
Process for Producing Compound [66] from Compound [63]
Compound [66] can be produced by reacting compound [63] with a peracid in a solvent.
Peracid: m-chloroperbenzoic acid or peracetic acid
Amount of peracid: 1 mole to an excess per mole of compound [63]
Solvent: halogenated hydrocarbons such as dichloromethane; and organic acids such as acetic acid
Temperature: xe2x88x9220xc2x0 C. to room temperature
Time: a moment to 24 hours
Process for Producing Compound [67] from Compound [66]
Compound [67] can be produced by reacting compound [63] in the presence of a base in a solvent.
Base: potassium carbonate or the like
Amount of base: 1 to 2 moles per mole of compound [66]
Solvent: methanol, ethanol, or the like
Temperature: 0xc2x0 to 50xc2x0 C.
Time: a moment to 5 hours
Process for Producing Compound [68] from Compound [67]
Compound [68] can be produced from compound [67] according to the method in which the hydroxyalkyl group in position 2 on the dihydrobenzofuran ring is replaced with another substituent, as described in U.S. Pat. No. 5,411,935, columns 5-10.
This is the production process according to the following scheme: 
wherein W1 is halogen, preferably chlorine; R32 is hydrogen or C1-C5 alkyl; and X, Y, Z2, R1, R2, R3, R11, R12, R33, and R34 are as defined above.
Process for Producing Compound [69] from Compound [42]
Compound [69] can be produced by reacting compound [42] with a halogenating agent such as thionyl chloride in a solvent according to the ordinary method.
Process for Producing Compound [70] from Compound [69]
Compound [70] can be produced by reacting compound [69] with a compound of the formula: 
wherein M⊕ is an alkali metal cation, preferably lithium cation or sodium cation; and R19, R22, and R32 are as defined above, to give a compound of the formula: 
wherein X, Y, R1, R2, R3, R19, R22, and R32 are as defined above, and then hydrolyzing and decarboxylating compound [75].
The first reaction is usually effected in a solvent. The reaction temperature is usually in the range of xe2x88x9220xc2x0 to 50xc2x0 C., preferably room temperature. The reaction time is usually in the range of a moment to 72 hours.
Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; acid amides such as formamide, N,N-dimethylformamide, and acetamide; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof.
The second reaction is effected in the presence of sulfuric acid, hydrobromic acid, or the like in a solvent such as a lower carboxylic acid, e.g., acetic acid, or without any solvent. The reaction temperature is usually in the range of 80xc2x0 to 140xc2x0 C., preferably 100xc2x0 to 120xc2x0 C. The reaction time is usually in the range of a moment to 72 hours.
Process for Producing Compound [71] from Compound [70]
Compound [71] can be produced by reacting compound [70] with a compound of the formula:
H2Nxe2x80x94Oxe2x80x94R33xe2x80x83xe2x80x83[76]
wherein R33 is as defined above.
The reaction is effected in a lower alcohol such as methanol, ethanol or isopropanol, or in a mixed solution of such a lower alcohol and water. The reaction temperature is in the range of 0xc2x0 to 80xc2x0 C. The reaction time is in the range of a moment to 72 hours.
Compound [76] can be used in the form of a free base or an acid addition salt such as a hydrochloride salt or a sulfate salt.
The above reaction can also be effected with the addition of a basic catalyst such as an organic base, e.g., pyridine; an alkali metal carbonate, e.g., sodium carbonate, potassium carbonate or the like; alkali metal hydrogencarbonate; or alkaline earth metal carbonate.
Compound [71] can also be produced by reacting a compound of the formula: 
wherein X, Y, R1, R2, R3, and R32 are as defined above, with a compound of the formula:
xe2x80x83R33xe2x80x94Dxe2x80x83xe2x80x83[78]
wherein R33 and D are as defined above, in the presence of a base, usually in a solvent.
Examples of the base which can be used include alkali metal alcoholates and alkali metal hydrides such as sodium hydride.
The amounts of the reagents to be used in the reaction, although the proportion of about 1 mole of compound [78] and 1 to 2 moles of the base to 1 mole of compound [77] is ideal, can be free changed depending upon the reaction conditions.
Examples of the solvent which can be used include ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; acid amides such as formamide, N,N-dimethylformamide, and acetamide; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; and mixtures thereof.
The reaction temperature in the above reaction is in the range of xe2x88x9210xc2x0 to 100xc2x0 C., preferably 0xc2x0 to 80xc2x0 C. The reaction time is in the range of a moment to 72 hours.
Process for Producing Compound [72] from Compound [70]
Compound [72] can be produced by reacting compound [70] with a compound of the formula: 
wherein R11 and R12 are as defined above.
The reaction is effected in a lower alcohol such as methanol, ethanol or isopropanol, or in a mixed solution of such a lower alcohol and water. The reaction temperature is in the range of 0xc2x0 to 80xc2x0 C. The reaction time is in the range of a moment to 72 hours.
Compound [79] can be used in the form of a free base or an acid addition salt such as a hydrochloride salt or a sulfate salt.
The above reaction can also be effected with the addition of a basic catalyst such as an organic base, e.g., pyridine; an alkali metal carbonate, e.g., sodium carbonate, potassium carbonate or the like; alkali metal hydrogencarbonate; or alkaline earth metal carbonate.
Process for Producing Compound [73] from Compound [70]
Compound [73] can be produced by reacting compound [70] with a compound of the formula:
R34xe2x80x94Z2Hxe2x80x83xe2x80x83[80]
wherein Z2 and R34 are as defined above, usually in the presence of a catalytic amount to an excess of an acid such as p-toluenesulfonic acid, hydrochloric acid or sulfuric acid, in an organic solvent such as benzene or chloroform.
The reaction temperature is in the range of xe2x88x9230xc2x0 C. to the boiling temperature of the reaction mixture. The reaction time is in the range of a moment to 72 hours.
This is the production process according to the following scheme: 
wherein Q1 and R1 are as defined above.
Compound [82] can be produced by reacting compound [81] with a compound of the formula: 
wherein R19 and R22 are as defined above, in a solvent.
The reaction temperature is usually in the range of 30xc2x0 to 120xc2x0 C., preferably 40xc2x0 to 80xc2x0 C. The reaction time is usually in the range of 5 to 72 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of compound [83] to 1 mole of compound [81] is ideal, can be changed depending upon the reaction conditions.
Examples the solvent which can be used include tertiary amines such as triethylamine.
After completion of the reaction, the reaction solvent is distilled out from the reaction mixture and the residue is subjected to chromatography, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired compound of the present invention can be isolated.
This is the production process according to the following scheme: 
wherein B3 is OR35, SR35, COOR35, COR16, or CR17xe2x95x90CR18COR16 (wherein R35 is (C1-C6 alkyl)carbonyl C1-C6 alkyl (C1-C6 haloalkyl)carbonyl C1-C6 alkyl, {(C1-C4 alkoxy)C1-C4 alkyl}carbonyl C1-C6 alkyl, or (C3-C8 cycloalkyl)carbonyl C1-C6 alkyl; and R16, R17, and R18 are as defined above); B4 is a substituent derived from B3 by protecting its ketone or aldehyde moiety with an alcohol; and X, Y, R1, R2, and R3 are as defined above.
Process for Producing Compound [100] from Compound [99]
Compound [100] can be produced in the same manner as described in Production Process 1, except that compound [99] is used in place of compound [4].
Process for Producing Compound [101] from Compound [100]
Compound [101] can be produced by deprotecting the ketal or acetal moiety of compound [100] by the ordinary method.
Compound [99] can be produced in the same manner as described below in the production process for compound [4], except that the ketone or aldehyde moiety in the substituent B3 of a compound of the formula: 
wherein X, Y, and B3 are as defined above, is protected with an alcohol such as methanol to give a compound of the formula: 
wherein X, Y, and B4 are as defined above, and compound [103] is used in place of compound [91] as described below.
Compound [5], which is one of the starting compounds in the production of the present compounds by production process 1, can be obtained from commercial sources or can be produced, for example, according to the method described in Jikken Kagaku Kouza (Maruzen K. K.), 4th ed., Vol. 24, pp. 259-260.
Compound [4], which is the other starting compound used in production process 1, can be produced by reacting a compound of the formula: 
wherein R1 and R3 are as defined above; and V is iodine, bromine, or chlorine, with water in the presence of a base to give a compound of the formula: 
wherein R1 and R3 are as defined above (hereinafter referred to as reaction 1), and then reacting compound [85] with a compound of the formula:
Q1xe2x80x94NHNH2xe2x80x83xe2x80x83[86]
wherein Q1 is as defined above (hereinafter referred to as reaction 2).
Compound [85] can also be reacted as its hydrate or acetal derivative in water or an alcohol.
Reaction 1 is usually effected in a solvent. The reaction temperature is usually in the range of 20xc2x0 to 100xc2x0 C. The reaction time is usually in the range of a moment to 24 hours. The amounts of the reagents to be used in the reaction, although the proportion of 2 moles of water and 2 moles of a base to 1 mole of compound [84] is ideal, can be changed, if necessary.
Examples of the base which can be used include organic bases and inorganic bases such as sodium acetate and potassium acetate.
Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; acid amides such as N,N-dimethylformamide; tertiary amines such as pyridine, triethylamine, diisopropyl-ethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; water; and mixtures thereof.
Reaction 2 is usually effected in a solvent. The reaction temperature is usually in the range of xe2x88x9220xc2x0 to 200xc2x0 C. The reaction time is usually in the range of a moment to 72 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of compound [86] to 1 mole of compound [84] used in reaction 1 is ideal, can be freely changed depending upon the reaction conditions. If necessary, the hydrochloride salt or sulfate salt of compound [86] can also be used.
Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; fatty acids such as formic acid, acetic acid, and propionic acid; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; water; and mixtures thereof.
After completion of the reaction, the reaction mixture is filtered to collect the crystals, which may be precipitated by the addition of water, if necessary, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.
Among the examples of compound [4], a compound of the formula: 
wherein X is as defined above; Y2 is halogen; and B2 is hydrogen, halogen, C1-C6 alkoxy, or C1-C6 alkylthio, can also be produced according to the following scheme: 
wherein X, Y2, B2, and R22 are as defined above.
Process for Producing Compound [89] from Compound [88]
Compound [89] can be produced by reacting compound [88] with a nitrite salt in hydrochloric acid or sulfuric acid to convert it into a diazonium salt, and then reacting the diazonium salt with a compound of the formula: 
wherein R22 is as defined above, in the presence of a base such as sodium acetate or pyridine.
(see, e.g., Tetrahedron, Vol. 35, p. 2013 (1979))
Process for Producing Compound [90] from Compound [89]
Compound [90] can be produced by hydrolyzing compound [89] usually in the presence of a base in a solvent.
The reaction temperature is in the range of 0xc2x0 to 150xc2x0 C., preferably 20xc2x0 to 100xc2x0 C. The reaction time is in the range of 1 to 24 hours, preferably 1 to 10 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of a base to 1 mole of compound [89] is ideal, can be changed, if necessary.
Examples of the base which can be used include inorganic bases such as potassium hydroxide, lithium hydroxide, barium hydroxide, and sodium hydroxide.
Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; nitro compounds such as nitromethane and nitrobenzene; acid amides such as N,N-dimethylformamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; water; and mixtures thereof.
Process for Producing Compound [87] from Compound [90]
Compound [87] can be produced by heating compound [90] in a solvent.
The reaction temperature is in the range of 50xc2x0 to 200xc2x0 C., preferably 50xc2x0 to 150xc2x0 C. The reaction time is in the range of a moment to 72 hours.
Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methytmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; fatty acids such as formic acid, acetic acid, and propionic acid; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; water; and mixtures thereof.
The above reaction can also be effected with the use of a metal, e.g., copper, as a catalyst.
After completion of the reaction, the reaction mixture is filtered to collect the precipitated crystals, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystalli- zation. Thus the desired compound can be isolated.
Compound [86] can also be produced by the following scheme: 
wherein Q1 is as defined above.
(see Organic Synthesis Collective, Vol. 1, p. 442)
Compound [91] is known in, or can be produced according to the method as described in, EP-61741-A; U.S. Pat. No. 4,670,046, U.S. Pat. No. 4,770,695, U.S. Pat. No. 4,709,049, U.S. Pat. No. 4,640,707, U.S. Pat. No. 4,720,297, U.S. Pat. No. 5,169,431; and JP-A 63-156787/1988.
Some examples of compound [91] can also be produced according to the following scheme: 
wherein R31 is COR16 or COOR10.
Process for Producing Compound [95] from Compound [94]
Compound [95] can be produced by reacting compound [94] with nitric acid in a solvent.
The reaction temperature is usually in the range of 0xc2x0 to 100xc2x0 C. The reaction time is usually in the range of a moment to 24 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of nitric acid to 1 mole of compound [94] is ideal, can be freely changed depending upon the reaction conditions.
Examples of the solvent which can be used include acidic solvents such as mixtures of nitric acid and sulfuric acid.
(see Organic Synthesis Collective, Vol. 1, p. 372)
Process for Producing Compound [96] from Compound [95]
Compound [96] can be produced by reducing compound [95] in a mixture of acetic acid, iron powder, and water.
The reaction temperature is usually in the range of 0xc2x0 to 100xc2x0 C. The reaction time is usually in the range of a moment to 24 hours.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired compound can be isolated.
(see Organic Synthesis Collective, Vol. 2, p. 471, and ibid., Vol. 5, p. 829)
The present compounds have excellent herbicidal activity, and some of them exhibit excellent selectivity between crop plants and unfavorable weeds. In particular, the present compounds have herbicidal activity against various unfavorable weeds as recited below, which may cause trouble in the foliar treatment and soil treatment on upland fields.
Polygonaceae:
wild buckwheat (Polygonum convolvulus), pale smartweed (Polygonum lapathifolium), Pennsylvania smartweed (Polygonum pensylvanicum), ladysthumb (Polygonum persicaria), curly dock (Rumex crispus), broadleaf dock (Rumex obtusifolius), Japanese knotweed (Polygonum cuspidatum)
Portulacaceae:
common purslane (Portulaca oleracea)
Caryophyllaceae:
common chickweed (Stellaria media)
Chenopodiaceae:
common lambsquarters (Chenopodium album), kochia (Kochia scoparia)
Amaranthaceae:
redroot pigweed (Amaranthus retroflexus), smooth pigweed (Amarantilus hybridus)
Crusiferae:
wild radish (Raphanius raplianistriol), wild mustard (Sinapis arvensis), shepherdspurse (Capsella bursa-pastoris)
Leguminosae:
hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia), Florida beggarweed (Desmodium tortuosum), white clover (Trifolium repens)
Malvaceae:
velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa)
Violaceae:
field pansy (Viola arvensis), wild pansy (Viola tricolor)
Rubiaceae:
catchweed bedstraw (cleavers) (Galium aparine)
Convolvulaceae:
ivyleaf morningglory (Ipomoea hederacea), tall morningglory (Ipomoea purpurea), entireleaf morningglory (Ipomoea hederacea var. integriuscula), pitted morningglory (Ipomoea lacunosa), field bindweed (Convolvulus arvensis)
Labiatae:
red deadnettle (Lamium purpureum), henbit (Lamium amplexicaule)
Solanaceae:
jimsonweed (Datura stramonium), black nightshade (Solanum nigrum)
Scrophulariaceae:
birdseye speedwell (Veronica persica), ivyleaf speedwell (Veronica hederaefolia)
Compositae:
common cocklebur (Xanthium pensylvanicum), common sunflower (Helianthus annuus), scentless chamomile (Mairicaria perforata or inodora), corn marigold (Chrysanthemum segetum), pineappleweed (Matricaria matricarioides), common ragweed (Ambrosia artemisiifolia), giant ragweed (Ambrosia trifida), horseweed (Erigeron canadensis), Japanese mugwor (Artemisia princeps), tall goldenrod (Solidago altissima)
Boraginaceae:
field forget-me-not (Myosotis arvensis)
Asclepiadaceae:
common milkweed (Asclepias syriaca)
Euphorbiaceae:
sun spurge (Euphorbia helioscopia), spotted spurge (Euphorbia maculata)
Gramineae:
barnyardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis), giant foxtail (Setaria faberi), large crabgrass (Digitaria sanguinalis), goosegrass (Eleusine indica), annual bluegrass (Poa annua), blackgrass (Alopecurus myosuroides), wild oat (Avena fatua), johnsongrass (Sorghum halepense), quackgrass (Agropyron repens), downy brome (Bromus tectorum), bermudagrass (Cynodon dactylon), fall panicum (Panicum dichotomiflorum), Texas panicum (Panicum texanum), shattercane (Sorghum vulgare)
Commelinaceae:
common dayflower (Commelina communis)
Equisetaceae:
field horsetail (Equisetum arvense)
Cyperaceae:
rice flatsedge (Cyperus iria), purple nutsedge (Cyperus rotundus), yellow nutsedge (Cyperus esculentus)
Furthermore, some of the present compounds have no problematic phytotoxicity on main crops such as corn (Zea mays), wheat (Triticum aestivum), barley (Hordeum vulgare), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), cotton (Gossypium spp.), sugar beet (Beta vulgaris), peanut (Arachis hypogaea), sunflower (Helianthus annuus) and canola (Brassica napus); garden crops such as flowers and ornamental plants; and vegetable crops.
The present compounds can attain effective control of unfavorable weeds in the no-tillage cultivation of soybean (Glycine max), corn (Zea mays), and wheat (Triticum aestivum). Furthermore, some of them exhibit no problematic phytotoxicity on crop plants.
The present compounds have herbicidal activity against various unfavorable weeds as recited below under the flooding treatment on paddy fields.
Gramineae:
barnyardgrass (Echinochloa oryzicola)
Scrophulariaceae:
common falsepimpernel (Lindernia procumbens)
Lythraceae:
Rotala indica, Ammannia multiflora 
Elatinaceae:
Elatine triandra 
Cyperaceae:
smallflower umbrellaplant (Cyperus difformis), hardstem bulrush (Scirpus juncoides), needle spikerush (Eleocharis acicularis), Cyperus serotinus, Eleocharis kuroguwai 
Pontederiaceae:
Monochoria vaginalis 
Alismataceae:
Sagittaria pygmaea, Sagittaria trifolia, Alisma canaliculatum 
Potamogetonaceae:
roundleaf pondweed (Potamogeton distinctus)
Umbelliferae:
Oenantlle javanica 
Furthermore, some of the present compounds have no problematic phytotoxicity on transplanted paddy rice.
The present compounds can attain effective control of various unfavorable weeds in orchards, grasslands, lawns, forests, waterways, canals, or other non-cultivated lands.
The present compounds also have herbicidal activity against various aquatic plants such as water hyacinth (Eichhornia crassipes), which will grow in waterways, canals, or the like.
The present compounds have substantially the same characteristics as those of the herbicidal compounds described in the publication of International Patent Application, WO95/34659. In the case where crop plants with tolerance imparted by introducing a herbicide tolerance gene described in the publication are cultivated, the present compounds can be used at greater doses than those used when ordinary crop plants without tolerance are cultivated, and it is, therefore, possible to attain effective control of other unfavorable plants.
When the present compounds are used as active ingredients of herbicides, they are usually mixed with solid or liquid carriers or diluents, surfactants, and other auxiliary agents to give formulations such as emulsifiable concentrates, wettable powders, flowables, granules, concentrated emulsions, and water-dispersible granules.
These formulations may contain any of the present compounds as an active ingredient at an amount of 0.001% to 80% by weight, preferably 0.005% to 70% by weight, based on the total weight of the formulation.
Examples of the solid carrier or diluent may include fine powders or granules of the following materials: mineral matters such as kaolin clay, attapulgite clay, bentonite, terra alba, pyrophyllite, talc, diatomaceous earth, and calcite; organic substances such as walnut shell powder; water-soluble organic substances such as urea; inorganic salts such as ammonium sulfate; and synthetic hydrated silicon oxide. Examples of the liquid carrier or diluent may include aromatic hydrocarbons such as methylnaphthalene, phenylxylylethane, and alkylbenzenes (e.g., xylene); alcohols such as isopropanol, ethylene glycol, and 2-ethoxyethanol; esters such as phthalic acid dialkyl esters; ketones such as acetone, cyclohexanone, and isophorone; mineral oils such as machine oil; vegetable oils such as soybean oil and cotton seed oil; dimethylsulfoxide, N,N-dimethylformamide, acetonitrile, N-methylpyrrolidone, water, and the like.
Examples of the surfactant used for emulsification, dispersing, or spreading may include surfactants of the anionic type, such as alkylsulfates, alkylsulfonates, alkylarylsulfonates, dialkylsulfosuccinates, and phosphates of polyoxyethylene alkyl aryl ethers; and surfactants of the nonionic type, such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters.
Examples of the auxiliary agent used for formulation may include ligninsulfonates, alginates, polyvinyl alcohol, gum arabic, carboxymethyl cellulose (CMC), and isopropyl acid phosphate (PAP).
The present compounds are usually formulated as described above and then used for the pre- or post-emergence soil, foliar, or flooding treatment of unfavorable weeds. The soil treatment may include soil surface treatment and soil incorporation. The foliar treatment may include application over the plants and directed application in which a chemical is applied only to the unfavorable weeds so as to keep off the crop plants.
The present compounds can be used, if necessary, in combination with other compounds having herbicidal activity. Examples of the compounds which can be used in combination with the present compounds may include various compounds described in Catalog 1995 Edition of Farm Chemicals Handbook (Meister Publishing Company); AG CHEM NEW COMPOUND REVIEW, VOL. 13, 1995 (AG CHEM INFORMATION SERVICE); or JOSOUZAI KENKYU SOURAN (Hakuyu-sha). Typical examples of such compounds are as follows: atrazin, cyanazine, dimethametryn, metribuzin, prometryn, simazine, simetryn, chlorotoluron, diuron, dymuron, fluometuron, isoproturon, linuron, methabenzthiazuron, bromoxynil, ioxynil, ethalfluratlin, pendimethalin, trifluralin, acifluorfen, acifluorfen-sodium, bifenox, chlomethoxynil, fomesafen, lactofen, oxadiazon, oxyfluorfen. carfentrazone, flumiclorac-pentyl, flumioxazine, fluthiacet-methyl, sulfentrazone, thidiazimin, difenzoquat, diquat, paraquat, 2,4-D, 2,4-DB, DCPA, MCPA, MCPB, clomeprop, clopyralid, dicamba, dithiopyr, fluroxypyr, mecoprop, naploanilide, phenothiol, quinclorac, triclopyr, acetochlor, alachlor, butachlor, diethatylethyl, metolachlor, pretilachlor, propachlor, bensulfuron-methyl, chlorsulfuron, chlorimuron-ethyl, halosulfuron-methyl, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, sulfometuron-methyl, thifensulfuron-methyl, triasuifuron, tribenuron-methyl, azimsulfuron, cloransulam-methyl, cyclosulfamuron, flumeturam, flupyrsulfuron, flazasulfuron, imazosulfuron, metosulam, prosulfuron, rimsulfuron, triflusulfuron-methyl, imazamethabenz-methyl, imazapyr, imazaquin, imazethapyr, imazameth, imazamox, bispyribac-sodium, pyriminobac-methyl, pyrithiobac-sodium, alloxydimsodium, clethodim, sethoxydim, tralkoxydim, diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl, fluazifop-butyl, fluazifop-p-butyl, haloxyfop-methyl, quizalofop-p-ethyl, cyhalofop-butyl, clodinafop-propargyl, benzofenap, clomazone, diflufenican, norflurazon, pyrazolate, pyrazoxyfen, isoxaflutole, sulcotrione, glufosinate-ammonium, glyphosate, bentazon, benthiocarb, bromobutide, butamifos, butylate, dimepiperate, dimethenamid, DSMA, EPTC, esprocarb, isoxaben, mefenacet, molinate, MSMA, piperophos, pributycarb, propanil, pyridate, triallate, cafenstrol, flupoxam, and thiafluamide.
The following will describe typical examples of such a combination, where the present compounds are designated by their compound numbers shown in Tables 1 to 5.
1. A mixture of one compound selected from the group consisting of compounds 1-495, 1-496, 1-499, 1-503 and 1-577, and one compound selected from the group consisting of atrazin, cyanazine, bromoxynil and bentazon at a weight ratio of 1:1 to 100.
2. A mixture of one compound selected from the group consisting of compounds 1-495, 1-496, 1-499, 1-503 and 1-577, and one compound selected from the group consisting of clethodim, sethoxydim, dichlofop-methyl, quizalofop-p-ethyl, lactofen, acifluorfen, acifluorfen-sodium, fomesafen, flumiclorac-pentyl and dicamba at a weight ratio of 1:0.5 to 50.
3. A mixture of one compound selected from the group consisting of compounds 1-495, 1-496, 1-499, 1-503 and 1-577, and one compound selected from the group consisting of nicosulfuron, primisulfuron. prosulfuron, chlorimuran-ethyl, thifensulfuron, rimsulfuron, halosulfuron, oxasulfuron, isoxaflutole, imazethapyr and imazamox at a weight ratio of 1:0.1 to 10.
4. A mixture of one compound selected from the group consisting of compounds 1-439, 1-482, 1-486, 1-496, 1-1076, 1-1123 and 1-1441, and one compound selected from the group consisting of isoproturon and chlorotoluron at a weight ratio of 1:1 to 100.
5. A mixture of one compound selected from the group consisting of compounds 1-439, 1-482, 1-486, 1-496, 1-1076, 1-1.123 and 1-1441, and one compound selected from the group consisting of mecoprop, fluroxypyr and ioxynil at a weight ratio of 1:0.5 to 50.
6. A mixture of one compound selected from the group consisting of compounds 1-439, 1-482, 1-486, 1-496, 1-1076, 1-1123 and 1-1441, and one compound selected from the group consisting of diflufenican, metsulfuron-methyl, fenoxaprop-ethyl and clodinafop-propargyl at a weight ratio of 1:0.1 to 10.
7. A mixture of one compound selected from the group consisting of compounds 1-1141, 1-1222 and 2-203, and one compound selected from the group consisting of glyphosate, glufosinate-ammonium and paraquat at a weight ratio of 1:1 to 100.
Moreover, the present compounds may also be used in admixture with insecticides, acaricides, nematocides, fungicides, plant growth regulators, fertilizers, soil improver, and the like.
When the present compounds are used as active ingredients of herbicides, the application amount is usually in the range of 0.01 to 10,000 g, preferably 1 to 8000 g, per hectare, although it may vary depending upon the weather conditions, formulation type, application timing, application method, soil conditions, crop plants, unfavorable weeds, and the like. In the case of emulsifiable concentrates, wettable powders, flowables, concentrated emulsions, water-dispersible granules, or the like, the formulation is usually applied at a prescribed amount after diluted with water having a volume of about 10 to 1000 liters per hectare, if necessary, with the addition of an adjuvant such as a spreading agent. In the case of granules or some types of flowables, the formulation is usually applied as such without any dilution.
Examples of the adjuvant used, if necessary, may include, in addition to the surfactants recited above, polyoxyethylene resin acids (esters), ligninsulfonates, abietates, dinaphthylmethanedisulfonates, crop oil concentrates, and vegetable oils such as soybean oil, corn oil, cotton seed oil, and sunflower oil.
The present compounds can also be used as active ingredients of harvesting aids such as defoliants and desiccating agents for cotton, and desiccating agents for potato. In these cases, the present compounds are usually formulated in the same manner as the case where they are used as active ingredients of herbicides, and used alone or in combination with other harvesting aids for foliar treatment before the harvesting of crops.